Sodium Carbonate → HCID 58574318, compound

HRID 1619400Notes

Reaction equation

HRID 1619400 reaction equation
O=[C:2]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:9]([O:11]C)=O.[Br:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCCl>[Br:13][C:14]1[CH:19]=[CH:18][N:17]2[C:9](=[O:11])[C:3]3[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:2]=3[N:20]=[C:16]2[CH:15]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 288225Methyl 2-oxocycloheptane-1-carboxylateHCID 6932822-Amino-4-bromopyridine

Product 1

HCID 58574318HCID 58574318, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of methyl 2-oxocycloheptanecarboxylate (2 g, 11.8 mmol) and 4-bromopyridin-2-amine (2.04 g, 11.8 mmol), and PPA (5 mL) in 1,2-dichloroethane (10 mL) was stirred at 85° C. for 5 h. The reaction mixture was cooled to ambient temperature. A chilled saturated sodium carbonate solution was added to adjust pH to 8. The resulting mixture was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. After filtration and concentration, the crude product was purified by silica gel chromatography to produce 2.4 g of the desired product. MS (ESI): 293 (MH+).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionThe resulting mixture was extracted with ethyl acetate (2×100 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration and concentration
  6. customthe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7821c82344c340d1882bdbd44321c820
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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